Jason Allen is pretty sure ChatGPT can come up with a better legal strategy than he can.
Mr. Allen, 42, who is serving a life sentence for murder at a maximum-security prison near Baltimore, has considered filing a lawsuit over the frequency of inmate cancer screenings there. He’s heard enough about ChatGPT to seek its help — but inmates aren’t allowed to freely browse the internet, much less fiddle with artificial intelligence.
So Mr. Allen called a friend outside the prison, Jessup Correctional Institution, who asked ChatGPT to outline potential legal arguments. The friend sent screenshots of the chatbot’s answers through the prison’s messaging system. Mr. Allen received them about a week and a half later, after approval by the correctional staff.
“A.I. is a tool that could assist people with finding justice. It could put pressure on them to do the right thing,” Mr. Allen said in a phone interview. “I’m still in the Stone Ages.”
Prisons have long restricted inmates’ access to technology, concerned they could use it to break the rules or commit crimes. The internet is mostly off limits, along with A.I.-powered chatbots.
But as hype about the technology has infiltrated prison yards and cellblocks, many inmates are eager to try it out. They’re attending workshops and classes to learn about A.I. They ask friends to send printouts of chatbot answers by snail mail. Some inmates even use contraband cellphones to gain access to the technology.
The result? A.I.-generated legal documents, essays, business plans and even a bespoke board game or two.
“The guys inside are really thirsty for knowledge about A.I.” said Kenyatta Leal, executive director of a nonprofit, Next Chapter, which helps former prisoners land jobs in the tech industry. “Those who know how to build and deploy A.I. will be the architects of the future.”
Others argue it’s too dangerous because prisoners could use it to break the rules or even plan an escape.
“This technology has way too many risks,” said Mike Thurmer, a board member of the U.S. Deputy Wardens Association who served as a prison warden in Wisconsin. “We had many inmates even abuse the phone system during my years.”
Mr. Leal recently led a workshop on A.I. at the San Quentin Rehabilitation Center in California for roughly 60 inmates. They peppered Mr. Leal, who served 19 years of a life sentence for possessing a gun as an ex-felon before his release in 2013, with questions about how A.I. works.
“We are in the dinosaur age in prison,” one inmate who attended the workshop wrote on an anonymous feedback form shared with The New York Times. “We need AI ACCESS,” wrote another.
For teaching his entrepreneurship class at the Utah State Correctional Facility in Salt Lake City, Michael Ulibarri asks ChatGPT about his students’ projects and brings paper printouts of its responses for discussion. He said his students hoped they could eventually use tech to bring their business ideas to fruition.
“Their technology is capped at a tablet,” said Mr. Ulibarri, an instructor at Defy Ventures, a nonprofit that helps people prepare for life after prison. “I think tech is their biggest disadvantage, the way we’re trending.”
But some law enforcement experts say it would be difficult to control prisoners’ wider access to technology.
“Open access to A.I. could allow those in prison to bypass communication monitoring, and they could plan illicit activities or access harmful information,” said Kimora, a prison educator and professor at the John Jay College of Criminal Justice. “Let’s face it: You and I probably believe it would be nice if we took care of people and were compassionate, but some people in prison are not that way.”
At Jessup, a compound of squat brick buildings dotted with security towers and surrounded by layers of barbed-wire fencing, inmates get limited access to tablets for monitored messaging, calls and vetted content like news articles and the radio.
The state prison, which holds people convicted of serious crimes like rape and murder, prohibits A.I. access “to protect institutional security, prevent misuse of communications technology and safeguard the public, staff, victims and those in our custody,” said Yianni Varonis, a spokesman for Maryland’s public safety and correctional services department.
That hasn’t stopped prisoners from trying. Some have secretly modified their tablets to get access to the internet, according to three people with knowledge of the prison, who requested anonymity to discuss rule-breaking behavior that could result in discipline. One inmate, who sells movies to other inmates after downloading them on an illegal cellphone, tried using A.I. to add subtitles to foreign films, one of the people said.
“Allegations of staff or incarcerated individual misconduct are taken with the utmost seriousness and are promptly reviewed through established investigative procedures,” Mr. Varonis said in a statement. The department had no evidence that any tablets had been “altered or manipulated,” he added.
Other inmates have found workarounds within the rules.
Nick Browning, a 34-year-old inmate at Jessup who has been incarcerated for murder since he was a teenager, first had the chance to use A.I. last October, on a prison-sanctioned video call with a lawyer.
“He took a screenshot of me and rendered it like a Van Gogh,” Mr. Browning said in a phone interview. “It was so cool to see.”
A.I. can be practical, too. Mr. Browning, who earned a master’s degree in business while incarcerated, helps teach a financial literacy class at the prison. One of the other instructors, also incarcerated, asked his sister to use A.I. to design an educational board game in the style of the Game of Life for the class, complete with a custom logo.
“We’ve all used A.I. this way because it’s the only way we can get access to it,” said Mr. Browning.
Tony Fleming, a 59-year-old at Jessup who is serving a life sentence for murder, wants to start a nonprofit to support incarcerated people re-entering society. So he messaged chatbot prompts to his sister from his tablet.
She pasted the instructions into ChatGPT, asking it to design a detailed plan for the nonprofit. She mailed him back the 17-page response.
“I don’t even know how to go on A.I., but she did it for me,” Mr. Fleming said. “I’ve been here for 30 years. I don’t know if she types it or scans it. I don’t even know how to use a computer.”
Jessup charges inmates 45 cents for every 15-minute phone call and 20 cents for incoming text messages. That adds up when attempting A.I. access.
When Mr. Allen tried to write his legal complaint to press for more cancer screenings, he said, he spent about $10 — equivalent to a week’s worth of wages from his work as a prison peer counselor.
He spent weeks calling and messaging friends because some fellow inmates believed they had developed prostate cancer after Jessup didn’t provide timely screenings.
(Mr. Varonis, the Maryland public safety and correctional services spokesman, said that the prison gives prostate cancer screenings based on individual risk factors. It adheres to “the same clinical protocols and standards followed by physicians in the broader community,” he added.)
Mr. Allen eventually gave up after burning through the cash his family had sent him to make phone calls. He was also straining his relationship with some friends.
After three or four phone calls, one asked, “Are you really my friend, or are you just using me for A.I.?” Mr. Allen said.
Alain Delaquérière contributed research.
https://www.nytimes.com/2026/04/21/business/ai-chatbots-prisoners.html
